White to light yellow liquid
Ethyl 2-chloropyrimidine-5-carboxylate is used in the synthesis of Retinoid x receptor agonists (RXR) that are used in the treatment of cancers.
A mixture of 1,2-Dihydro-2-oxo-5-pyrimidinecarboxylic acid ethyl ester (3.60 g, 21 mmol), phosphorus oxychloride (25 mL), and N, N-dimethylaniline (2.5 mL) was heated to reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml) and extracted with EtOAc. After work, the residue was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 5 per cent v/v) to give the product Ethyl 2-chloropyrimidine-5-carboxylate (1.20 g, 30 per cent).
[1] Patent: US9249156, 2016, B2. Location in patent: Page/Page column 34
[2] Patent: WO2018/85342, 2018, A1. Location in patent: Page/Page column 26; 27; 28
[3] Patent: US2009/76006, 2009, A1. Location in patent: Page/Page column 31; 40
[4] Patent: WO2011/130628, 2011, A1. Location in patent: Page/Page column 138-139
[5] Patent: WO2009/36016, 2009, A1. Location in patent: Page/Page column 69
